Amos Kennedy Jr.: From Corporate Analyst To Modern-Day Artisan

Amos Kennedy Jr.: From Corporate Analyst To Modern-Day Artisan

At age 40, Amos Kennedy Jr. walked into a printing demonstration while on vacation in Colonial Williamsburg in Virginia and fell in love with a letterpress. Within five minutes, he decided to quit his job as a Chicago-based systems analyst for AT&T and become a printer.

He studied at the University of Wisconsin-Madison, and eventually moved from the Midwest to Alabama and settled for a far less lucrative income—to the tune of $7,000 a year—but what he felt was a more satisfying vocation and lifestyle. Now in his 60s, Kennedy has made a name for himself as a first-rate printer and artist, although he dislikes the word artist and instead says he’s someone who “makes stuff.” But his talent—along with his distinctive uniform of overalls and a pink dress shirt—has made him a leader in his field who can’t be ignored. In 2012, filmmaker Laura Zinger made a documentary, Proceed and Be Bold!, capturing Kennedy’s artistry, activism, and irreverence, as well as serving as a window into the life of an artisan in modern-day America.

Kennedy’s greatest contribution, however, might be his insistence on living a life of his choosing, one with low overhead that enables a healthy balance of work and play. He subscribes to the idea that all humans should do what they can to be happy, and that the “pursuit of happiness” is not an American luxury but a must for humanity. “Following your bliss and being happy is a human trait,” Kennedy says. “I think it being corrupted is a trait of advanced civilization because you have to corrupt it in order for people to submit to advanced civilization—what we call an advanced civilization.” 99U spoke with Kennedy about his dramatic midlife career change, how the issue of race significantly impacts his work, and what it’s like being a craftsman working by hand today.


Kennedy Jr. photographed in his letterpress studio and throughout his Detroit, Michigan neighborhood.

Proceed and Be Bold! is an excellent title for your documentary. Do you suppose you would have inspired a film had you stayed at AT&T?

I would have inspired a performance of Death of a Salesman.

Or Death of a Systems Analyst! Your decision to dedicate yourself to printing is a kind of variation on the American dream—chuck everything, financial security be damned, and do what you love. Was there any fear in that decision or did you feel you had no choice?

I actually think it is the American dream, because the people who originally colonized the United States, they dropped everything and took off someplace where they didn’t know where they were going to live or survive.

Five minutes with a letterpress changed everything, but you could have just as easily found your calling that day in blacksmithing or apothecary. What was it about printing?

I had studied calligraphy for a very long time, about 10 years, but I wasn’t good at it. The letterpress appealed to me because I was attracted to books. I love letters; I love books. It was a way of working with letters, making books, and also the fact that you can make multiple copies.

Can you describe the conversation in your head during those five minutes?

What I was thinking was, I got to find a place in Chicago where I can learn this.

I love what you said at the end of the documentary, that all you have to do to have your life is “declare yourself crazy, and do what you want to do.” Why do you suppose that’s so hard for people?

Because we have been taught all our lives that we have to work for somebody else. We have to have security. Again, I think it was my generation, and even now, we have this model of working forever for somebody and then retiring and going off to play golf. And that’s the good life. We aren’t taught to be independent and free, although we scream that we’re an independent and free nation. We talk about personal responsibility, but personal responsibility is first for your happiness. That happiness comes from finding that internal peace, and I think a lot of people don’t find that. That’s how come you have these substitutions that are accepted by larger society, such as consumerism or the sports fanatic. These sort of things. The people are trying to find a good substitute, but that freedom that we so long for is, basically, an ability to express ourselves and just be happy.

You have—and have had—many admirers and apprentices. Your son Adric prints, too. What are you teaching them besides printing?

I think I’m just showing them that there’s an alternative lifestyle, that pursuing what makes you happy will do exactly that. With that comes a lifestyle that you can be comfortable with. I will never own a Mercedes-Benz, but that’s okay. I don’t need a Mercedes-Benz. I have something else. Because I think a lot in this nation and civilization… a lot of consumerism, it’s like what they say about a heroin junkie. You get that high. It goes away. You can function for a little bit, but then you got to go get that high again. But each high is just a little less high than the last one. I really think consumerism functions at that level in this society.


I read the paper by Andrew Steeves, “Print! Amos Kennedy, Jr. & the Fine Art of Rabblerousery.” He wrote that “at first your work appears to be chaotic and accidental.” Can you describe what you’re doing?

What I am doing is actually mimicking my world vision. The vision of what I think is the world. It can be very easily summed up in the snowflake. No two snowflakes are the same. No two of my posters are really the same. It speaks to the individuality of each person; the uniqueness. They are unique on their own when you take time to look at just one, but if you look at them collectively, they are equally as beautiful.

What I am doing is actually mimicking my world vision. The vision of what I think is the world.

Your former professor, Walter Hamady at the University of Wisconsin, he’s known for many things, including his book series The Interminable Gabberjabbs, and his use of satire and poking fun. It seems you found in him a kindred spirit.

I did. He is a master craftsperson. He pays great attention to detail, and his work is very intentional. This is one of the things that I’ve learned, and he is a very irreverent person. And that’s part of his talent … people either love him or hate him.

Gabberjabbs influenced your NappygRams [negroes in art collection], right?

They did in one respect, but he just questioned things. He questioned and he explored. The NappygRams started out purely as a political statement, as a manifestation of a frustration I was experiencing [while teaching] at Indiana University. The first NappygRam was “Affirmative Action is a Joke.” I was just tired of it. I was just tired of what we think about affirmative action; the critics of affirmative action. The fact that if it was really working then we wouldn’t be having this discussion 20 years later.

Which brings me to the fact that you don’t shy away from politics in your work. It’s a major part of what you do. Would you say activism was always part of your life, or really only since you started “making stuff”?

I tell people, I’m always a person who will disagree with everybody. Sometimes for fun, but a lot of times because I just saw that there was an injustice somewhere. I would challenge teachers when the normal people would not. Or the way that they would challenge them would be in some rough, traditional way. I would just challenge them on the point.

You play a lot with race, identity, and perception in your work and in yourself, i.e. calling yourself a “humble negro printer,” being “Mr. Overalls” and using racially charged images like Sambo and Aunt Jemima. Are you successful as a provocateur, and what are you hoping to accomplish?

I think I am successful to a point, and what I’m hoping to accomplish is to change people’s perceptions of these things. The racially charged images are actually paying homage to the fact that these were images that were used. We cannot whitewash our history, OK? We have to look at it, and say, “Wow, this is what happened.” One of the most racially charged, hatefully charged images is the swastika, but you see it all the time. But the sun sign is what the swastika was based upon… People say, Oh I can’t put that up because it’s the swastika.” There was once a saying that if you want to sell a book, put the swastika on the cover and you would sell another 10,000.

You go to India, you see it everywhere. It means something entirely different.

Right, right. How is it that one political party can take a sign for less than 50 years and turn it into, we don’t even want to see this anymore. That sign that has been around for millennia. But the swastika we see all the time. This is in one way a racist act. In one way we’re praising the Nazis but damning the Indians who had the sign, and that sign is universal. It’s a very primitive sign. You find it in African cultures. You find it in European cultures. It was everywhere in the United States before WWII.


And you feel you’re making your point?

Yes, it is being made and it’s being made slowly… it’s reclaiming. It is very much like the word black. In the ’50s, people who were descendants of African slaves did not really want to be called black. But in the ’60s, we reclaimed that word and turned it into something beautiful. Black is beautiful.” Black Power.” That is similar to what I’m doing. That’s one reason why I use the term negro, because it is offensive to people. I use the term “ni***r,” and I tell people that’s not my problem that they labeled it that. This is a word, and so I claim it. Right now I say that I am a negro, but technically I am a descendant of the enslaved peoples of this civilization because I want to reclaim my heritage of being enslaved. So when you look at me, you remember that this nation was built on the labor of enslaved people. Honor my ancestors and the sacrifice that they made that you can live in the wealth that you think you have.

And on the flip slide, you’ve eschewed the wealth you could have had in that civilization to go do the work you do.


Your family left the Deep South for Michigan when you were still a kid. When you started printing, you moved to Alabama for a while, and a few years ago you settled in Detroit. Why did you leave the South once again for the Midwest?

I needed an airport. I do a lot of traveling, and so I needed to be close to an airport because my traveling was requiring me get up at two o’clock in the morning, drive 90 miles to the airport, and then take the early flight. Air travel was taking the entire day.

You couldn’t have moved near Atlanta?

Well, Detroit was the only city that I could live in at the lifestyle I had. I could move to Atlanta, but I would have to work harder, and I think that would ruin my relationship with the work that I do. I tell students if what you want to do is print, you find the place where you can afford to print more.

You raised beyond $30,000 to meet your mark for the Detroit Printing Plant, the print shop, the book bindery, and the handmade paper mill that you have wanted to have built in Detroit. What is the status? Is this fully operational at this point?

No. Unfortunately Detroit, I tell people, believe the hype but don’t believe the hype. I thought I could roll in there, three months later have a building and boom—six months it would be up and running. It didn’t work that way. The status now is that we have secured a building. We changed the name of the project to simply the Printing Plant, the Printery of the Americas. We’re a 501(c)(3). We’ve also secured a house for people to live in, and a plot of vacant land for a garden. And now I’m on phase two. Those funds have been depleted, but we are going forward because I found a new source of some funds to allow for the occupation of the building.

Would the occupants be apprentices?

I would not call them apprentices. There will be people who want to explore their relationship with letterpress printing. To have an apprentice means I would have to make money, and I am at the point now where I want to make as little money as possible. I will have to earn money for the renovation of the building. That means I’m going to have to work much harder. That’s a cause I want to do. I don’t want to say, Janice is dependent upon me paying her $2,400 this month so she can have her rent and she can live her life.” I’m willing to make a big capital investment, but the ongoing maintenance should go to the building.

You have said you print because you’re good at it. You have also said that your goal was to be a master printer. Are you there yet?

No. I still have a long way to go. There’s a lot to learn, and I have seen people who move with great fluidity through the print shop, through the whole process. It is almost an effortless motion. It’s like water going down a creek, very slowly, very gently. Like watching a leaf float down the river.

And that’s how you’ll know? How does anyone know when they are that and when they’ve mastered something? Can they see it in themselves?

I believe that they can. I am hoping that I will be able to say, I am now at the point where I can really learn. And let me just add that at this point in my career, I do not believe that I am mastering the craft so much as I am allowing the craft to explain the workings of the universe—the workings of the universe and the connections that make the universe flow.

from 99U99U

If I Had To Do It All Over Again

If I Had To Do It All Over Again

You hear it all the time: “Everything happens for a reason.” Let it sit there for a minute. Marinate. Steep. What exactly prompted that thought? You flunked a class. You got fired. You presented a really wacky idea in a pitch meeting when something more conservative would have won the gig. Regrets. We all have ‘em.

Does everything really happen for some indefinable reason? Probably not. Call it a defense mechanism, something you say when you’ve screwed up and you need a way to move on. But sometimes we need to live with our mistakes. Own them. How else will we remember not to make them in the future? A little wallowing, as long as it’s not paralyzing, never hurt anyone.

So we decided to throw this query out to designers of all stripes, from leaders at Airbnb and Shake Shack to those guiding bold studios like La Tortilleria: If you could look back at your career and rethink one of your big decisions, what would it be? And why?

Sure, we wanted to hear about the do-overs, but our main premise wasn’t to make anyone dredge up unpleasant moments. Rather, our goal was to have them weigh the choices they made then, based on what they know now.  We were looking to commiserate. We were looking for a little wisdom. We got both.

Laura Seargeant Richardson

Creative director, Argodesign / Austin, Texas

I would have trusted my instincts and drawn every damn day.

I would recognize that the future is by our design, but some things never change and that is the ability to communicate our ideas across mediums. Because we rely on the visual medium more than any other, I believe it has the greatest weight and importance to the design profession. My instinct was to take art in high school. At the time, my mom suggested typing or writing…something more “practical,” in her mind. That was before the internet and touch screens and a world we had not imagined. I remember my first interview with the VP of creative at frog design. I was applying for an interaction design position. When I decided to show my versatility by sharing a few visuals, like a T-shirt design, he asked me, “Are you applying to be a visual designer?” I said no. He replied, “Then don’t show me that stuff.”

Design consultancies sell expertise, and they often have specific design roles. At the time, visual and interaction design were very much separate, and I was clearly in the interaction design camp. We “didn’t do” visual design. So, while I was at one of the most esteemed design firms, I did not improve any of my visual design skills. Instead, I became an expert in the field of interaction design as well as design research and strategy. However, my greatest regret is not taking the art path. I think some of the strongest designers are a combination of art and science. And while I have an eye for design, while I can creatively direct designers of all types, I can never bring my ideas to visual life in a gratifying way. For a designer, that is the most painful and frustrating limitation. People can hear me, but they cannot see me. If I had to do it all over again, I would trust my instincts and draw every damn day.

Zita Arcq

Creative director and cofounder of La Tortilleria / Monterrey, Mexico

I wouldn’t have worked for companies that didn’t completely trust us.

Last year I went to a master class with Bob Gower, who teaches responsive organizational design. He mentioned something really simple but important: If people are not kind, you don’t want to work with them. That is something our firm forgot twice in the past, once five and then again three years ago. Both times, we were caught thinking that a large client and large account would be a good thing for the agency. That was a big mistake. We realized that sometimes large companies don’t know how to work with agencies. They don’t know how to collaborate. All they want to do is impose. And it begins at the top, with owners or heads of companies not really knowing how their people manage their teams or the people they work with.

They don’t realize this affects the entire organization. Both times we completed our work obligations. But one of those times someone from our agency quit because she couldn’t handle the client anymore. She didn’t want to be in touch every day with this person because the client was too much work and too exhausting. If the client had been nice, kind, conscientious, the work would have been just work, instead of a nightmare. We now have a couple things that we think about before deciding to work with a new client. First, do we have contact with the person who makes decisions for the organization? If we do not, we need to be sure the person we are working with has the power to make decisions. Otherwise you will not be able to do good work. Then you have to decide if this person, the contact person within the client’s organization, knows how to work and collaborate. If they don’t trust you, don’t let them hire you.

Alex Schleifer

VP of design, Airbnb / San Francisco, California

I would have picked my projects more carefully.

Look, we all have to do this as a designer – just take a job sometimes. I know that. But in the past, I think there were months and years that maybe I lost some of the drive because I was working on projects and for companies that I didn’t believe in. It’s good training when you’re starting out to say yes to everything. However, there’s a time when you start to negotiate with yourself about saying yes all the time. The internal conversation changes because something you fell in love with becomes the worst part of a job. Sometimes you’re using all that creative energy on companies and projects you don’t believe in. Working with people you might not really like all that much can be draining.

It’s hard for me to want to change those decisions, because I’m very happy today. I do feel that I could have saved myself a couple of years here and there if I’d just told myself, This is not what I want to be doing. So just make sure that you don’t fall out of love with designing something because you are not designing it in ways that enrich you. Working enough to be able to say “I don’t love this project” is a nice problem to have. Lots of people out there are thrilled to get the gigs they do get. But falling out of love with design can happen to anyone.

Syd Weiler

Illustrator, animator, and Adobe creative resident / Sarasota, Florida

I was told that I should think about a different career, something that was not creative.

I’m just starting out, having graduated last May from Ringling College of Art and Design in Sarasota, Florida, so I’m not entirely sure I can answer this question well. I’m not even 24, after all. But I did make a big mistake in school. For a few years I was in an animation curriculum, and I almost failed out. Well, failed sounds too severe, but my grades weren’t good enough to continue in the program. How did I get into that situation? I was trying to force myself to do work I thought, and others were telling me, was valuable. Sometimes I wish I had listened to my gut and switched majors to illustration earlier, because it would have saved me a lot of emotional turmoil.

But, I wonder if, had I done that, would I have learned the lessons I live by today?

I came out of high school in northern West Virginia, where I breezed through school and never failed at anything. I was accepted into this prestigious program and, two years later, I was struggling. Before that point, I never had the feeling of not being good at something I was trying really hard to do well in. The curriculum demanded a certain style, a form-and-volume-based drawing style.  When I wasn’t able to make it work that way, I was simply told I was wrong, without any other explanation.

It’s the first time I felt like my style wasn’t a good fit for the program. After all, I was getting the feedback from professors via their critiques and my grades that it wasn’t working out. I was even told that I should think about a different career, something that was not creative. I was a wreck!

So here I am a few years later, and I’m an illustrator and an animator. The Adobe creative residency program plucked me out and has been sponsoring me for nearly a year and will continue to April. It wasn’t until I switched over to illustration that things began feeling more comfortable for me. All along, I knew it would be a better fit, but there was this stigma at school that illustration was for the weak, that it was the easy way out.

It wasn’t until a classmate made the switch that I realized I could switch, too. In the end it added up to another year of school, but it was worth it. I started rebuilding myself and my work from the ground up, because I had a clean slate and a fresh start. I now make work about what I like, by doing it how I like to make it. I’m building an online community (my streaming channel) around this idea, for others who might not have a good working or educational space, like I didn’t for a long time. I can do what I do now because of what I learned in both animation and illustration.

Cathie Urushibata

Art director, Shake Shack / New York City

I rationalized the excuse due to cost and timing, but in reality I was just scared.

If I had to do it all over again, I would have studied abroad for a semester as an undergrad at Cal State Long Beach. I was a fine arts and illustration major. We had opportunities to study abroad in places like Italy. I could imagine myself drawing and painting in front of an original Michelangelo. At the same time, the required art history course I was taking covered the Italian Renaissance. I picked up some pamphlets and did some research; it seemed like the perfect opportunity.

But once I learned how much more expensive it would be to travel abroad and that it would delay my graduation, I didn’t go through with it. In my head, I made excuses – too expensive and not the right time. In reality, I was just scared. 

I moved to New York City for grad school and got some experience being on my own. After that, I didn’t want to miss another opportunity to travel abroad. When I started to freelance, I realized I could work remotely – from my apartment in New York or somewhere else. That’s when I knew I had to take advantage of the opportunity. I started to tell my friends that I planned to go to Paris for a month. By putting it out there, it made me accountable. In September 2011, I traveled to Paris for a month and even went to Morocco for a long weekend.

Looking back, I should have stayed longer! Traveling and challenging myself to be in an environment that was new to me was one of the best things I could have done personally and creatively. It is always inspiring to see what other creatives are doing out there in their own city, even if they can’t get on a plane for Europe. Of course, you should go to the local art museums. But there’s something to learn from walking the aisles of the grocery store, checking out the packaging. Now whenever I have the opportunity to travel, I make sure to take it.

Rob Vargas

Creative director, Bloomberg BusinessweekNew York City

I would have still sacrificed my personal life at times to jump-start my career.

There was a certain point earlier in my career where I was basically sacrificing almost all of my time to work, and I didn’t have a lot of time for friendships and relationships and things like that. Some people might say they regret that, but I actually don’t. Early in your career, you’re proving yourself, and you just have to work five times as hard. There were days where I’d work a full day at one job, then come home, lock myself in my room and work on two other freelance client projects. Partly that’s because you have to work like crazy to make ends meet in an expensive city like New York. But also, I never considered myself naturally talented.

When I was an associate art director at New York, I worked my first 24 hours straight. The magazine is known for these immersive infographics, and I had to design a four-page infographic on my own. I remember very distinctly being in the office one day and then it was 7:00 a.m. [the next day] and no one was in the office yet. And I was like, I need to get out of here before someone sees me. Working extremely hard is always a risk. If I was out in the streets or something, I would have been like, Oh man, I wish I had spent more time with my friends. How I wound up at Bloomberg Businessweek is an amazing stroke of luck. But obviously I owe some of that to all the work that I did. So yeah, I do feel in a lot of ways happy that I put in the time.

Cedric Kiefer

Cofounder, onformative / Berlin, Germany

I used to think that a concept would be more valuable the longer I worked on or thought about it.

The biggest piece of advice I have for someone who is faced with an important decision is don’t hesitate if it feels right. Take the example of how we started onformative. My cofounder, Julia Laub, and I decided to start the studio seven years ago without having met in person. We had been talking online for about a year, but never worked together or spent more than a day in the same room. Still, we had the feeling that there was an opportunity for us if we moved quickly.

That was a big decision for me, since I moved to Berlin from the south of Germany and founded onformative a few months later. Maybe it was a bit naive of me to decide to move so quickly back then, but I think if we had thought about it too long, we might have missed our chance.

The idea of not overthinking something can apply to everything from a big decision, like moving across Germany to start a business, to making new hires and even working on individual projects.

If you think about ideas or concepts, they’re not necessarily going to improve the longer you think about them. That was a hard thing for me to learn, because earlier in my career, I used to think that a concept would be more valuable the longer I worked on it. After a while, you learn that the simplest idea is usually the best one. Remember, just because a project feels easy for you doesn’t mean it feels easy for someone else. A lot of the time that’s just proof of why you’re doing the work you’re doing.

Irene Au

Design partner at Khosla Ventures / Menlo Park, California

Although I was continually diving into the unknown, I grew, and I had a ton of fun.

After I graduated with my master’s degree in industrial engineering and human-computer interaction, the advice some people gave me was to join an established company, like Hewlett-Packard, to learn the ropes and then go on to a company that had a higher risk and higher reward factor. But I decided to become an interaction designer at Netscape, which had only started two years earlier. My friend’s parents told me they couldn’t believe what I was doing by choosing Netscape over a Hewlett-Packard, and that I was making the wrong choice. However, I knew that my life didn’t have time to wait. If I had gone to work at HP at the time, I would have missed my window of opportunity at Netscape. When I reflect on my career, this is a theme that I have seen play over and over again – diving in to build something that has never been built before. That is my tribe, and those are my people – right in the middle of where it feels like the action is happening, even if people looking in from the outside can’t fully understand my decision. When I was looking for my next job after Netscape, I chose between Yahoo!, Excite, Webvan, and a couple of design firms. I chose Yahoo! because they had the best mind-set for making the internet useful and accessible to everyone. The company was filled with fun, smart people who had a lot of heart and genuinely cared about serving the people who used the site. Most of my design peers, though, thought of Yahoo! as a Web directory that lacked any design. They didn’t see that Yahoo! was a useful place to start your internet experience, that it could grow into something more interesting and bigger, and they couldn’t understand why I would want to join the company, because it didn’t obviously value design.

Yahoo! proved to be a great career move for me. No other internet company was using human-centered design practices to conceive and create their services, and my boss gave me tremendous leeway to lead our efforts and figure out how to do this on internet time, at internet scale. Yahoo! became the premier destination for people all over the world on the internet. We redefined what it meant for a product to be well-designed – it wasn’t just about aesthetics but, more importantly, the extent to which it solved people’s needs and was easy to use.

My decisions to join Google after Yahoo!, then Udacity, then Khosla Ventures were all motivated in the same way:  go where I can work with great people, follow my curiosity, and choose the path with the most heart. When I get asked for career advice now, these are the same factors that I ask people to consider.

Each experience we have in life, each challenge we accept, sets us up for the next endeavor we take on. My experience at Yahoo! taught me how to build and scale design teams and understand at a deep level the impact organizational design has on a company’s product design. At Google, I learned how to operate in a bottom-up, engineering-driven environment, so that we could engage engineers and product managers to think like designers. At Udacity I gained tremendous empathy for early-stage startups and their occasional need to pivot while they find product-market fit. These experiences have equipped me with perspective and insight that allow me to add value to the Khosla Ventures portfolio as a design partner.

If I had to do it all over again, I would take the same journey. Although I was diving into the unknown with no guarantees of what the future would hold, I learned something from each experience. I grew, and I had a ton of fun.

from 99U99U

Gemma O’Brien: The Future of Typography is Human

Gemma O’Brien: The Future of Typography is Human

By now Australian calligrapher Gemma O’Brien is used to being watched. The creation of her large-scale, hand-drawn murals has evolved into live theater where she not only focuses on the end result, but also performs for an audience of strangers who pause to view her work-in-progress. Sometimes that means the crowds are literally standing two feet behind her, as she carves out the word adaptation in bold blue, red, and white colors inside a hotel ballroom at the 2016 AIGA Conference. Other times, that can mean they’re gawking from the street, like when she was hoisted into the air by a crane to paint the last of 37 Kirin cider billboards displayed across her native Australia in 2013. Even when raised up in the air, O’Brien still wasn’t alone – by rule, a crane operator joined her in the cabin for safety reasons. 

This kind of art creation, one that is documented to show that, yes, indeed, a real person was responsible for what you see in front of you, is the driving force behind’s O’Brien’s belief that the future of typography is human. For as much as people relish the way technology can allow us to escape, there is no escaping the need for a human connection, and why artists who show their processes develop a following that is interested in their work – and them. 


O’Brien photographed in and around Sydney, Australia.

O’Brien likens live art to sport. “You can’t just look away,” she says. While an artist, like an athlete, can practice a concept to try and perfect it, the actual performance forces an artist to take a leap into an environment where mistakes can’t be airbrushed out. That, O’Brien argues, leads to the most authentic self of a design, one that can’t be second-guessed or reviewed later with the benefit of hindsight. Rather, it’s purely created in the moment.       

Still, even the most spontaneous act can actually be well-rehearsed with a known outcome. Because when the camera and crowds are watching, there is little to no room for error. And when O’Brien is fulfilling substantial commissions for the likes of Adidas, Qantas, and Volcom, she knows the result has to look brand perfect.

We recently sat down with O’Brien, who has been working as an independent commercial artist based in Sydney since 2012, to discuss why authenticity trumps perfection, how she balances artistic freedom with the requirements of brand work, and why she prefers to work at night.

What’s a hand letterer’s role, your role, in the world today?

Within the field of typography, you have such a diverse range of professions and people doing different things. There’s a lot of type designers who are designing the fonts that we need to read efficiently. My work is more in this category of looking at words and thinking of them as art or bringing them into a picture as themselves. That can be to create a beautiful image or add new meaning to words – connecting people in a way that they might connect with illustration or art, as opposed to just the printed word.

How did you notice this pendulum swing from a digital landscape that showed essentially just the finished type or the work to one that brought the human element back to typography?

I started noticing that whenever the illustrations I posted on Instagram had a human element – like me painting or drawing, or even just the textures and tools that I drew with – in them, then it got so much more of a viewer response than if it was only an image. It showed the human scale of someone painting, and people were aligning with that. I think it’s partly that it’s enjoyable to watch humans working.

You’ve compared the live element of making art to sport. As people watch you, there’s a sheer wonder if you’re going to be able to complete your mural without making a mistake, like how someone watches tennis players rally and wonders who will hit the ball out first.


When did you starting drawing this comparison between art and sport? 

When I started thinking about this idea of authenticity and how it has played out in the last few years, and then when authenticity became an overused buzzword. I started reading about the ways it was described, and writers were talking about either music, theater, or sport. Then I thought how it applies to art and design as well. Although design was never really imagined in that capacity, because by the time the design is at the point when the viewer sees it, there have been so many revision stages beforehand. It’s almost like crafting authenticity, because the performance part of it is done in the same way people in theater practice their play before the show or sports people train. As a calligrapher, you practice all the strokes before you actually create something. So the art is perfect, but because the imperfections or the mistakes have been removed from the process along the way. Now, artists are starting to bring design back to something that’s a bit more of a lived-in, real experience.

What does this mean for the world of design? Stop trying to make everything look so perfect? 

Yes. A lot of the jobs that I started to get off the back of this trend of creating large-scale murals were this fake version of the real thing. Brands might want to do this fabricated chalkboard for the background of a TV commercial, but then the process that went into making it look like it was spontaneous was a little bit deranged or over-planned. Brands like McDonald’s were suddenly bringing out “authentic” chalkboard burger ads, but they’re making them too derivative and forced.

How do you then balance the freedom you want to create something organically with meeting the requirements of the job the brand commissioned you for?

The instances where I find myself the happiest or most creatively satisfied with the work is when I’ve taken a period of time to experiment with either different tools or a new illustration style or scale, and with no constraints in terms of a budget or a timeline. And then that becomes the example for the client to look at and say, Ah, this is what we want. At least by the time that it’s then taken into a commercial context, the idea actually had the time that it needed to come to fruition creatively.

Being videotaped while painting or drawing is practically a requirement for your brand work these days. How do you feel about being videotaped while you create?

It really depends. There’s nothing that I like more than being locked in a gallery by myself overnight to paint because I feel the most relaxed. Nobody is watching me and nobody is filming, and I can make creative decisions in the same way that I would on a sketchbook, but on the walls. Whereas, when it’s a live painting for a brand or even at a conference, I specifically plan out something I can make that I know is achievable.

So you win no matter what.

Yes. It is, in a way, orchestrated spontaneity. I know that it is a lot more difficult to be completely free and creative when there’s a camera this close. At the same time, it forces me to really focus on the artwork, because I have to block everything else out in a Zen state. I can feel when people are there watching, but I’ve gotten better at it from having to do it all the time.


Photo by Christoper Morris


Photo by Tal Roberts


Photo by Adriana Picker


What is your daily work schedule like when you’re at home in your attic office in Sydney? 

I’m not a 9-to-5 person. I never liked 9-to-5, but I do have a rhythm that is pretty similar each day. If it’s sunny outside I’ll start my day by going for a bike ride or a swim to make the most of the day and then I’ll work overnight. Maybe from 4 p.m. to 2 a.m. or 3 a.m. A big block of time overnight will be where a majority of my work is made.

Why overnight?

Initially, it started because it was distraction-free. There were no emails or phone calls – though now I have an American agent, so there is no free time. I just feel like there is something about nighttime where I get in a less alert state, and that allows me to relax and do the work. It’s deadly quiet, and from the attic I can see the moon. Sometimes, if I have a really hard deadline, I can also see the sun come up. Whereas during the day, I’m very switched on. I’m good at doing phone calls or answering emails or maybe planning a budget or a timeline, that sort of thing. But I’m not so good creatively.

How does that work schedule sync with a social life?

I used to be a lot worse than I am now. I definitely used to be like, No, I have to work, and it’s so important. Now, I feel like I can definitely have the best of both worlds. Depending on what projects I’m working on, I’ll usually make time for friends and take breaks.

A big block of time overnight will be where a majority of my work is made.

What led you to stop pursuing a law degree and change careers to become a hand letterer?

I think the reason I studied law in the first place was probably a subliminal pressure from my secondary school to choose a “smart” career option because I got good grades. When I finally was in the midst of the law degree I realized that deep down I needed to be following a more creative path and could never really see myself as a lawyer. Once I had this realization, I knew I needed to make the switch from law to art or design. When I chose design, the field of graphic design was the closest thing to art that had a feasible career. So many designers say that. They either want to design a record cover for their favorite band or they want to be an artist – graphic design is the second-best option and I was probably in that category.

I didn’t discover typography until the first year of law school, and, even then I remember thinking that the idea of working every day only with lettering and typography was not possible. I didn’t know anyone that was doing that at the time and in the industry, there wasn’t anyone who was a letterer. It was pre Jessica Hische. No examples of people doing that. You were a graphic designer or in illustrator. I think the shift in my design degree also happened with the shift in the industry where typography and lettering really grew and the opportunity to just focus on that became a reality. Now, that is pretty much what I do.

What advice would you give an aspiring hand letterer trying to to break into the field?

I think five years ago you could have said, Get your work out there on a blog or on Instagram. Now, there are so many people on those channels that I don’t even know if that’s the right way. I have always believed that it has to be about the work first. If you spend the time finding what it is that is unique to you and focus on creating as much of the best work that you possibly can, at least then you have the groundwork to do more, whether it’s meeting the right person or working.

When I chose design, the field of graphic design was the closest thing to art that had a feasible career

What separates good work from not-good work? 

In the world of lettering, typography, and calligraphy, it’s difficult now, because a lot of young designers are learning about fonts and typefaces, but they are not learning about the history of calligraphy and writing, which informs “good” and “bad.” There is a fine line between being a really annoying designer who says this is not good because of this and this, and looking at the bigger picture by asking, What do people respond to? For me, that was a big jump to make. Going from, Okay, well it is important to know the history, but how people react on first impression also has value. Maybe it isn’t about being too tedious and specific about the rules but also finding balance between the rules and viewer response.

It’s like how someone who writes a classic book is held in higher regard than someone who writes a mass market paperback best-seller. They’re both good works, but they are judged differently.

Exactly. And you can’t discount something just because it’s popular. The Kardashians, for example. I always think, What is going on? But there must be something that people are connecting with. You can’t just be like, Everyone is stupid.


Your typographic work takes on many forms – calligraphic brushwork, illustrated letterforms, digital type, hand-painted murals, and even fine-point-pen drawings of puke puns on airplane barf bags. Why pursue different styles, even within the lettering family?

I know a lot of designers who think you need to have a style so that people know you for that, but I think that, especially within typography and lettering, the restraints of the alphabet are enough. I always wanted to show a different range of skills and styles within what I do, so that people were not pigeonholing me into one particular style.

Some of your greatest competition for jobs in the future might not be only your fellow artists, but from robots that can mimic hand movements and produce calligraphy. That’s freaky. How do you feel about this?

I find it interesting because I’ve started to think, What are the real applications for this? Other than the company in New York [Bond] where they are using robots to create handwritten notes.

Yeah, robotic, handwritten notes. That is an oxymoron.

Yes, I would never do that for anything other than the novelty factor. I’m curious to see if it does have a big audience and there are people who have robots write sentimental notes. I mean, what other applications would there be in daily use for a calligraphy robot?

Brands could hire a robot to do their hand-drawn work cheaper and faster?

Exactly. But then it takes away the value of it being done by hand. There is a Japanese robot that is interesting because it was taken to a Japanese school and used to teach some young Japanese students Japanese calligraphy, while a teacher was also there. I like the idea of that in the future. Imagine if we end up having some bionic arm on a human and then you could just download Gemma O’Brien’s Brush Lettering program and your bionic hand guides you through the letters. You wouldn’t need to come to my workshop. You just download the software into your bionic arm and then you get the pen and you can do it yourself. Could it go that far?

I have always believed that it has to be about the work first.

You’re traveling around the world for work, while you remain based in Sydney. Have you ever thought about leaving for a new creative environment, like New York City?    

In the last few years I’ve thought that maybe I should move to New York since it’s the thing for all of the creatives in Australia to do. But after seeing all these other cities I realized that I really liked Australia as a place to knuckle down and do the work in between all the travel. There is a small but growing creative community there with lots of amazing letterers, artists, and a street art scene. I actually got asked in an interview once, Gemma, all the best letterers are in Brooklyn. Why don’t you live there? Because so many styles are shared instantly online, being in Australia is the right place for me to create great work. It’s isolated, I don’t have any distractions, and being there allows me to tap into something creatively that’s completely unique to the rest of the world, my surroundings.

from 99U99U